Transforming Holiday Problems Into Holiday Blessings

by Dr. Les Wright, Jr.

The holidays are supposed to be “the most wonderful time of the year,” right? Yet every year—right on cue—clients show up to coaching sessions overwhelmed. With session topics covering navigating difficult relatives (including those who turn into political pundits), juggling office parties with coworkers you hardly recognize without their Zoom filters, and trying not to blow the budget or the waistband, the holidays can feel like an Olympic obstacle course wrapped in tinsel.

Add travel delays, last-minute shopping, and the gravitational pull of holiday desserts, and you’ve got the perfect recipe for stress. As Coaches— personal and professional, life, executive and leadership, spiritual, and business—we hear these stories constantly.

Here is the good news: Transforming holiday problems into holiday blessings often comes down to two deceptively simple steps:

1. Choosing what matters to you (your values)

2. Setting boundaries that protect what matters from what doesn’t

Today’s world feels heavy—economic pressure, workplace burnout, global uncertainty, and the lingering fear of “What if the world shuts down again?” When external stress is high, the holidays amplify whatever we’re already carrying.

So the essential question becomes this: How do we reclaim the holidays as a season of meaning instead of an emotional  roller coaster?

The answer returns to values and boundaries.

Choosing What Really Matters: Values Drive the Experience

The holidays are full of default traditions we follow because that is how things have always been done. When you slow down and ask yourself, “What do I want this season to feel like?” everything shifts.

For some, the value is connection, not chaos. For others, it’s rest, not running all over town. For many, it’s giving, but not at the expense of financial peace.

Example: One of my clients felt guilty skipping a large family gathering, even though she left every year emotionally drained. After identifying her top values—peace, authenticity, and quality connection—she chose a smaller gathering with loved ones who energized her. The result? She finally enjoyed her holiday instead of recovering from it.

Values become the compass. Once you know what matters most, decisions become easier—almost peaceful.

Setting Boundaries: Protecting What Matters

Boundaries are the grown-up version of saying, “No thanks, I’m full,” but for your soul.

Boundaries might look like the following:

• Declining invitations that drain you

• Setting a realistic gift budget and following it

• Requesting alone time before or after gatherings

• Saying, “I’d rather not discuss politics today”

• Choosing one dessert instead of the sampler (unless dessert is your value—then enjoy it fully!)

Here’s my little insight: When you safeguard what’s important, the holidays cease being something that happens to you and begin happening for you.

Final Thoughts: Your Holidays, Your Choice

The holidays offer a yearly reminder to appreciate life, savor connection, and slow down long enough to notice the blessings we often rush past. When you celebrate on autopilot, you risk missing it all.

Choose what matters. Protect it with boundaries. Give yourself permission to design a holiday season that feels like a blessing, not a burden.

You get to choose your life—and your holidays.

Wishing you a season filled with meaning, laughter, and peace.